Methyl acetoacetate → HCID 178429400, compound

HRID 2300828Notes

Reaction equation

HRID 2300828 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]([NH2:12])=[NH:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+].[C:16](OC)(=[O:21])[CH2:17][C:18]([CH3:20])=O>CO>[C:1]1([C@@H:7]([NH:9][C:10]2[N:12]=[C:16]([OH:21])[CH:17]=[C:18]([CH3:20])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 10942334Sodium MethoxideHCID 178462048HCID 178462048, compound

Product 1

HCID 178429400HCID 178429400, compoundYield 12.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of (S)-1-phenylethylguanidine (1 g, 6.13 mmol, 1 eq) [prepared by condensation of (S)-1-phenylethylamine with methylthiopseudourea sulfate in refluxing aqeous sodium bicarbonate] in methanol (5.8 mL) was added a solution of 25% NaOMe in MeOH (4.2 mL, 18.39 mmol, 3 eq). To this stirred solution was added methyl acetoacetate (0.66 mL, 6.13 mmol, 1 eq) dropwise via syringe. The mixture was allowed to stir overnight. The methanol was removed by warming under a flow of air. The residue was dissolved in 20 mL water, acidified with concentrated aqueous HCL and extracted with ether and the ether layer discarded. The aqueous layer was neutralized and extracted with ethyl acetate. The organic extracts were combined and dried over anhydrous Na2SO4, filtered and concentrated. The material was purified by flash column chromatography to give 181 mg of the title compound. Mass spectrum (NH3/CI): 230.2 (M+1).

Workup

  1. customThe methanol was removed
  2. temperatureby warming under a flow of air
  3. dissolutionThe residue was dissolved in 20 mL water
  4. extractionextracted with ether
  5. extractionextracted with ethyl acetate
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material was purified by flash column chromatography

Sources & evidence

ORD record
ord-d4991d45bc634029b00fd40ccf848324
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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